Hydrochloric Acid → HCID 57695593, compound

Participants

Reaction Conditions

Reaction Steps

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid benzyl ester (573 mg, 1 mmol) was dissolved in a mixture of THF (5 ml) and water (5 ml). LiOH (72 mg, 3 mmol) was added, and the resulting mixture was stirred at 90° C. overnight. After the reaction was complete, the reaction mixture was cooled to r.t., acidified with 1M HCl to pH=1. After extraction with Et2O (25 ml×3), the combined organics were washed with water and brine and dried over Na2SO4. After filtration and concentration, 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid was obtained as a white solid (463 mg, 96%). M.p.: 181-182° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.56-7.53 (m, 2H), 7.43-7.39 (m, 2H), 7.36-7.28 (m, 7H), 7.16 (dd, J=8.4, 2.0 Hz, 1H), 7.03 (d, J=2.0 Hz, 1H), 6.98-6.93 (m, 2H), 5.27 (s, 2H), 5.17 (s, 2H), 3.65 (s, 3H), 2.84 (hept, J=6.8 Hz, 1H), 1.17 (d, J=6.8 Hz, 6H); LCMS: 483 [M+1].

Provenance & Evidence